


Remain Cool, Winchester

by orphan_account



Category: Supernatural
Genre: Alternate Universe - High School, Fluff, M/M
Language: English
Status: In-Progress
Published: 2014-02-01
Updated: 2014-02-01
Packaged: 2018-01-10 19:20:16
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,603
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1163494
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Dean Winchester has had a huge (some would say obsessive) crush on Castiel for years. This is what happens when Dean finally does something about it.</p>
            </blockquote>





	1. Chapter 1

_He really shouldn’t be so friggin’ hot_ , Dean Winchester thought to himself as he leaned against his open locker door and watched Castiel walk down the hallway and toward their shared English class. _It doesn’t make any sense._

Dean had harbored a sick kind of interest in Castiel Novak for years. Something about a guy that just did not give a shit about what everyone else thought of him appealed to Dean. From the way he seemed to dress like he just rolled around in a pile of clothes and then stepped outside to the outrageous eye contact he kept with anyone that decided to look in his direction, Castiel just seemed utterly indifferent to what was deemed “socially acceptable.” It was way hotter than it had any right to be.

Or at least Dean thought so. He had thought so for a disgusting amount of time. But Dean never did anything about it. The fear of rejection was too great. Even when Castiel had declared, totally unashamedly, during a class discussion about sexuality in a Health class freshman year, that he was “completely indifferent to sexual orientation,” and basically confirmed that he was _at least_ in Dean’s ballpark, Dean hadn’t asked him out. Even when a seemingly endless line of girls and guys decided to hit on him, Dean hadn’t. He just stood by and watched while people took their shot at Castiel. Freakin’ brave bastards. Except, Castiel always turned them down. Dean wasn’t sure why, but he knew that if Castiel didn’t think people like Meg and Balthazar (who were both, Dean could begrudgingly admit, very attractive) were good enough for him, than he definitely wouldn’t think much of Dean. Besides, pining after someone unattainable was one thing; Dean could at least _pretend_ he had a chance in hell with Castiel. Asking him out was something totally different. There was a possibility of rejection then, and Dean was definitely not putting himself in that kind of position.

“Checkin’ out your man again, brother? Gettin’ to be a bit of a professional stalker at this point, aren’t ya?”

Dean leaped at the sudden interruption from his, admittedly creepy, checking out of the man of his dreams.

“Jesus Christ, Benny! Warn a guy before you come up behind him like a freakin’ ninja.” Dean said as he tried to calm his pounding heart and turned back to the inside of his locker to gather his things for class.

“Brother, I have been standin’ here for a good minute watchin’ you stare at Novak like he just saved your soul from eternal damnation. Has it occurred to you that maybe you should go use your mouth to talk to him instead of drool?” Benny replied.

“Ah, we’re discussing drool. I take it I have missed Dean’s first glimpse of Cas for the day, then?” Charlie questioned, pushing between the boys. “Pretty sure the stalking is reaching restraining order level at this point, Dean.”

Dean rolled his eyes in exasperation at his two best friends.

“It isn’t stalking. It’s a healthy appreciation of a beautifully made man. God did something right with that one, and it’s a sin to ignore finely crafted work.” Dean stated, rather proud of his ability to swing stalking into something that at least _sounded_ poetic.

“Oh, Lord, what a line. You got it so bad. I’m embarrassed on your behalf.” Charlie said, grinning. “Seriously, Dean, you should just talk to him. Remember before Gilda and I got together? And I said she was way too gorgeous to be human? And there was no way I could talk to her without puking? But now here we are, going strong for two whole years!” 

“Charlie, you met Gilda at a Con in eighth grade. She was dressed as a faery. She literally didn’t look human. You used the line ‘Hello, I’m hot. And you are?’ and she said that was so pathetic that you had to buy her lunch to make up for it.” Dean said, sighing. Charlie failed at an attempt to look abashed while Benny laughed. “And you!” Dean continued, pointing at Benny. Benny sobered immediately and began to pick at the hem of his Pirates football jersey. “You and Andrea have been together for, like, fifty years! The rules of dating have changed since you two got together. It isn’t kindergarten anymore. You can’t try to steal her toy boat during recess, have her punch you in the face, and then be together forever. The two of you can’t give me advice when your love lives are something out of some kind of cheesy Spanish soap opera.”

Having properly made his case about the unfairness of his situation, Dean shut his locker door and slammed his head against it. Out of the corner of his eye, Dean watched Charlie and Benny exchange a concerned glance. When they started playing rock paper scissors to decide who had to cheer him up, Dean sighed and turned to face them.

“Listen, guys, I appreciate the pep talk that hasn’t happened yet. I do.” They both tried to interrupt him, but Dean powered through. “So, can we skip it? You’re both destined to live happily ever after, while I’m destined to be alone forever with no one but my kid brother to keep me going. It’s cool. I’ve accepted it. You don’t have to worry about me. I’m fine. Now, I gotta go to English or Shurley’s gonna gimme detention for a week. I’ll see you at lunch.”

Dean threw them a tight smile, tossed his backpack onto his shoulder and walked away before they could say anything else. Dean knew he was overreacting, but it wasn’t even over Castiel. He just was irritated by the constant concern. He was fine. He didn’t need Castiel’s affection to be happy. He was a tough guy. He was fine. He was completely fine.

Dean was still thinking about how fine he was as he turned the corner into Shurley’s English class. And he was still thinking about how fine he was as his foot got caught on something and the world slipped in his vision and his whole body slammed into the floor with a thud. All of the breath left his lungs and the class erupted into giggles. Dean lifted himself onto his elbows and looked back to see Alistair grinning over him from his seat.

“Hello, Dean. Watch where you’re steppin’ next time, huh?” he said, grinning.

“Dick.” Dean replied under his breath as he started to lift himself off of the floor. As he did, his eyes became level with a hand. A hand that was connected to an arm that was connected to the body of Castiel Novak. Castiel’s head was cocked to the side and a small smile graced his face.

_Oh, God._ Panic racked Dean immediately. _No. Remain cool, Winchester. This is your moment. You got this._ Dean attempted to put a charming smile on his face. And then realized he was wasting his charm staring at Castiel’s hand. And not taking said hand. Just staring. And he was still doing it. _Shit._

Dean quickly grabbed Castiel’s hand and allowed him to pull Dean off of the floor. Suddenly, Dean was eye- to- eye with Castiel Novak, who had a knowing smile on his face like he could tell Dean was having a heart attack. Which might be possible. Castiel had a way of staring that felt like he could see directly into your soul.

“Um. Hey, Cas. How’s it goin’?” Dean asked, hesitantly. God, Castiel had the prettiest eyes. That color blue was just not natural. And they made it ridiculously hard to focus on the conversation they weren’t even having yet.

“My day is going very well, Dean. Especially considering I haven’t been slammed into the floor.” Castiel replied, glaring behind Dean at Alistair and his still laughing friends.

“No big deal, Cas. He just tripped me. I shoulda been paying better attention.” _Instead of thinking about how fine I am. Alone. Without you. What a load of shit. You wanna go out some time? Grab a burger? Cuddle while we watch Lord of the Rings?_ Dean shook himself. _Get a grip, Winchester, you are blowing this._ “’Sides, I’ll take care of him later.”

“And, of course, you will alert me as to when ‘later’ is so I can assist you.” Castiel said, firmly. He made air quotes with his fingers for the word ‘later.’ Which was adorable. But he was also still glaring at Alistair like he would smite him if he could.

And, boy, was that all manner of hot. Dean felt his body flush with warmth, especially his left hand. Which is not, strictly speaking, the area where that kind of heat normally centered. In fact, his hand was burning up and sweaty. Weird. Dean looked down and saw that- _Son of a bitch_ \- he was still grasping Castiel’s hand in his own. He immediately dropped Castiel’s hand as if it had burnt him and wiped his hand on his jeans to get the sweat off. Castiel looked at him with concern. _Smooth, Winchester._

Suddenly a shrill ring pierced Dean’s ears, signaling the beginning of class. Castiel gave Dean a small smile and returned to his seat. Dean quickly shuffled into the seat behind him and pretended to listen as Shurley started droning on about something.

And that was another problem with having an addictive crush on Castiel. Dean actually liked English class. He did well in it. He liked reading. But, God, did he have a hard time paying attention after Castiel transferred in during the second quarter. Especially considering Castiel had claimed the seat directly in front of Dean. Which meant Dean couldn’t very well ignore him. But he also couldn’t focus 100% on English when Castiel spoke so eloquently about how _Misery_ was a reflection of Stephen King’s fear of writer’s block that all Dean could think about was how much he wanted to hear every single thought Castiel had on the subject.

Not to mention that, from this vantage point, Dean could always stare at the back of Castiel’s body all class period and no one was the wiser. Today, Castiel had on a signature awful outfit: Black skinny jeans with a bright orange and purple sweater that was about two sizes too big and a red hoodie. Dean had to find out if he really did just pick out whatever clothes were lying around and put them on. And how he managed to still make everyone want him regardless of his truly hideous clothes.

Dean was still musing over the idea of Castiel just stopping by a Goodwill and throwing random articles of clothing in a bag when the bell rang.


	2. Chapter 2

After grabbing a burger, Dean headed towards his normal seat in the lunchroom with Ash, Benny, Charlie, and Jo. Jo and Benny were deep in a conversation about some sport thing that Dean couldn’t hope to understand, so he sat down next to Charlie as she continued to try to convince Ash that, with their combined talents, they could easily trick their way into the school’s main grading system and give themselves 4.0s.

“The fact that we already have high GPAs isn’t the point, Ash. It’s the principle of the thing. They make it too easy. If we don’t take advantage of their lapse in judgment then how will they ever learn to improve?” Charlie said to an unyielding Ash.

“I don’t know, dude. We can’t really afford to get caught messin’ with the system again. Plus, I was plannin’ on really getting some of the background stuff figured out on our game. That sounds a hell of a lot more fun than screwin’ with GPAs.” Ash said.

“Ugh, Ash, you are no fun. I’ll come help you with the game this weekend, though. A zombie hospital. How do we come up with this stuff?” Charlie asked, shaking her head and sighing. “So, Dean, how did Cas look today? Did you actually speak real words to him today? Real, honest to God, English words?”

Dean looked up from his sandwich with a glare.

“Well, I tried Klingon, but wouldn’t you know it, he isn’t fluent.” Dean sighed. “I actually did speak to him, though. He pulled me up off the floor after Alistair tripped me.”

“Well, that’s good. I’m very proud of you, Dean. Say, in any part of the conversation, did you, perhaps, invite him to sit with us at lunch?” Charlie said in a rush, looking behind Dean with wide eyes. 

“No, I’m not insane. Why do you-” The rest of Dean’s words were lost as he turned to see what Charlie was staring at and saw Castiel walking towards them. Dean quickly turned back to the table. “I think I’m gonna vomit. Quick, someone fake a heart attack.”

Ash made a move to grasp his chest, but Charlie slapped his hand down.

“No, no, no one is allowed to help Dean escape from this. He has got to man up and speak to his man like a man. Got it?” 

Ash frowned. “I actually think I’m more confused than befo-”

“Hello, Dean.”

Everyone at the table turned to gape at the dark haired man that stood next to the table. Or, at least, Dean assumed they all were. He really hadn’t been able to tear his eyes away from Cas’ to check. But Cas was staring back. That was a good thing, right? _God, his eyes- No! Don’t get hung up on them again! You have to focus on trying to start-_

It was then that Charlie kicked Dean in the shin, hard. After yelping in pain, he looked over to find her glaring at him. _Say something,_ she mouthed. Dean turned back to Cas, quickly.

“H-hey, Cas. How’s it goin’?”

“I am still very well, thank you. I was wondering if I could sit and have lunch with you today? If that’s alright?” Cas asked, gaze still locked onto Dean’s.

“Uh, I, um-”

“Of course you can, Cas! Jeez, Dean, manners! You can sit between Dean and I!” Charlie said, scooting over to allow just barely enough room for Cas. Dean wondered why that was until Cas sat down and Dean’s entire left side was melded to Cas’. _That's my clever girl. I owe you one._

“So, Cas, Dean was just telling us how you played the hero to our little damsel in distress this morning! Saving him from Alistair, you brave little soldier!” _Nevermind._

“I am not a damsel! I was fine. He just helped me off the floor.” Dean said, indignantly.

“Dean is correct. I simply offered him assistance. I’m sure he could have handled himself.” Cas said, biting into his cheeseburger. The look of ecstasy on his face mildly short-circuited Dean’s brain. “Although, Dean has promised to allow me to assist him in providing appropriate repercussions for Alistair’s actions whenever he sees fit.” 

“Aw, you’re gonna beat up people for him! That’s so romantic.” Charlie squealed, while everyone else at the table chuckled. Dean came to the realization that Charlie was only going to make this worse, so, he decided he would try to take control of the conversation. Any minute now. Any second. _Winchester, you are pathetic._

“I don’t see anything traditionally romantic in the concept. I suppose it depends on whether or not one finds the idea of a dominant, protective figure one of great sexual prowess.” Cas said completely straight-faced. At this, the whole table erupted into laughter.

“Whaddya say, brother? Do you find the idea of Cas here dominatin’ ya-”

“Okay, I feel like that is enough of whatever is happening here!” Dean said, his mind finally catching up with the conversation. “Um, so, Cas.” _Great start, Winchester, now if you could think of literally anything to say after that._ Cas was looking at him expectantly as the rest of the table attempted to go back to their previous conversations and Dean had nothing whatsoever to say. “What’s the word?” _God damn it! What the fuck does that even-_

“Well, Dean, I’ve been thinking. Monkeys are so clever. And they’re sensible in that they leave the peel on the bananas that they eat. Is it really necessary to test cosmetics on them? I mean, how important is lipstick to you, Dean?” Castiel asked Dean imploringly.

“Uh, not very.” Dean murmured, staring at Castiel’s chapped lips. “I had no idea that you cared so much about that kind of thing, Cas.”

“Animal welfare has always been very important to me. I attempted vegetarianism for a short period of time, but, unfortunately, my appreciation of red meat did not lend well to that endeavor. As you may have guessed.”

“Yeah, I did notice you seem to, uh, really like burgers.”

“Has it been an issue? I have been told before I am a bit exuberant in my affection for them.” Cas said, taking a bite of his burger. “It’s just- These make me very happy.”

Which was an understatement. Cas looked freakin’ ecstatic. Staring at Cas, who was just sitting there shoving his burger in his mouth with a huge smile, Dean could not think of anything else besides _I want to be around you all of the time._ And that pretty much broke him. They were in a crowded lunchroom, Charlie was pretty obviously listening in on everything they were saying, Cas was talking with his mouth full, and this was definitely not the time or place that Dean had ever imagined making his move, but he didn’t really think about any of that when he said:

“Hey, Cas, I know this place that has a burger and bacon happy hour. I could take you there sometime, if you want. Best burgers ever, I swear.”

Cas dropped his burger and stared at Dean with wide eyes and that was when the terror rushed back into Dean. _Shit. Oh, shit. Well, there you go, Winchester. You’ve ruined it. Jesus Christ._ Dean looked away as a blush rushed to his face and started to quickly pick up his tray so he could _get the hell out of there._

“I mean- uh, never mind, I’m sure you’re busy and, uh-” Dean was rambling nonsense while he attempted to push out his tray and pick up his seat and- _Wait, no, that isn’t right. Oh, who the hell cares? Just get out of here_ \- Dean felt a strong hand grasp his arm to keep him still as he attempted to stand.

“That would be great, Dean. I’m free after school today, if that works well for you?” Cas said, looking up at Dean.

Dean felt his whole body go slack and dimly registered that he had dropped back into his seat.

“Seriously?” Dean blurted out, his eyes wide.

“Absolutely. Unless, you were joking?” Cas asked, looking kind of shy for the first time in the whole exchange.

Dean felt a broad grin take over his face. _Whoa. We are not getting’ any points for execution, but damn. He said yes._

“No way! I’m one hundred percent serious! Well, maybe not about them being the best ever. There was this seaside place my family went to while we were on this road trip when I was seven and that was definitely the best burger I’ve ever had in my life, but these are a very close second. And they aren’t even from a cafeteria, so they’ll definitely be the best burger you’ve had all day, unless you ate one for breakfast this morning. Which doesn’t make any sense, I mean, why would you eat a burger for breakfast? Although, one time we were running low on groceries so I just ate some pie for breakfast, but it had fruit in it so I figured it counted as-”

At this point, Dean realized he was rambling, but Cas was just watching him talk with this serene little smile on his face. It made Dean’s stomach flip. Especially once he realized that Cas still hadn’t let go of his arm. When Cas saw Dean dazedly smiling down at where his hand grasped Dean’s arm, however, he quickly took his hand off of Dean and returned it to his lap.

“Um, but yeah. Completely serious.” Dean finished, a little out of breath and still smiling like an idiot. But Cas was smiling his little half smile, too, so Dean felt his giddiness was justified. Right then, the bell signaling the end of lunch rang and the people around them started to move around and leave the cafeteria. Dean’s heart started to pound in overdrive as the sudden activity popped their little bubble. “Uh, how about we meet by my car after school? I’ll drive?”

“That sounds lovely, Dean. I’ll see you then.” Cas said, slowly gathering his things and standing up. Dean handed him one of his notebooks that was still on the table and Cas reached to take it from him. Their fingers brushed against each other during the transfer. They stood there, just kind of staring and smiling at each other, sharing the hold on the notebook, until Charlie suddenly fake coughed from beside Dean. They both blushed and looked away from each other as Dean let go of the notebook. Cas muttered a thank you before walking off, while Dean watched him, sighing.

“Dean Winchester, you dog!” Charlie said, with a sly smirk. “So, how does it feel? How does it feel to finally grow a pair and act like a woman?”

“My brain feels fuzzy, my stomach feels like jello, I am never washing this arm again, and I am going to memorize the exact shade of his eyes so I can write dozens of poems about them.” Dean said, still in a daze.

“Ah, yes. Manhood. So regal, so strong, so masculine.” Charlie remarked, trying to keep a straight face.

“Shut up.” Dean said, as he swung his arm around her shoulders as they made their way to the hallway. “Stop trying to ruin my fantastic mood.”

“I’m not trying to ruin anything.” Charlie said through her giggles. “I’m just trying to find a good segue into asking if you really do find a dominant figure sexually attractive, because if so I feel like Cas is-”

“Alright, good mood gone! Thank you, Charlie!” Dean said, removing his arm from around her and quickly walking away.

“I’m just saying, he’s definitely got the whole secret badass thing goin’ on!” Charlie yelled after him, still laughing, as she headed in the opposite direction.

Several students turned questioning gazes at them, but Dean really couldn’t be bothered to care. He had a date. He had a date with Castiel Novak. He had a date with the guy he had been secretly stalking for years now. Dean stopped in the middle of the hallway, his smile fading. _I have a date with Castiel Novak. What the hell am I thinking?_


	3. Chapter 3

By the time the final bell rang, Dean was completely overrun with nerves. Now that he had had time to truly think about what he was doing he realized that he was not at all prepared to go on a date with Castiel, Object of His Affections Since Forever. He didn’t know what they would talk about. It was bound to be awkward. Castiel would probably find him boring or dorky and then never talk to him again. It was with this worried argument circling in his mind that he bee lined from his last class of the day to his baby brother’s locker.

“When we get to the car, I’m gonna need you to pretend that your appendix just ruptured.”

“Okay.” Sam said, not even looking up. “What for?”

“I accidentally asked Castiel Novak out and he said yes, so he’s waiting for me to meet him there.” Dean whispered.

“What?” Sam yelled, dropping his backpack. “You asked Cas out? Finally! Ash owes me five bucks.”

“No, no, you’re missing the point: This is a bad thing.” Dean said. “Wait, why does Ash owe you five bucks?”

“He said Cas would ask you out first, but I figured you’d have a nervous breakdown and blurt it out sometime. So, I won. How is this a bad thing?” Sam asked, picking his things up off of the floor and shutting his locker.

“Because I don’t know what I was thinking! And stop making bets about me!” Dean said as they made their way toward the parking lot. “No way I can actually go on a date with Cas. What will we talk about? What if he hates me? What if he thinks I’m weird?”

“Considering it’s you, I’m pretty sure he already thinks you’re weird. And you know he’s interested, Dean. He agreed to go on a date with you! All you have to do is act like you normally do.” Sam scrunched up his nose. “Actually, maybe act with a little more propriety. Be a gentleman. But also yourself. Combine the two.”

“It would make my life ten times easier if you would just pretend to be deathly ill.” Dean sighed. They stepped out the door of the school and Dean scanned the parking lot for his baby. His car was parked right where he left her this morning, and beside her was Cas, who was covered by a huge trench coat and facing the Impala. All the calm Dean had gained from talking with Sam left him. “Shit, shit, shit. I can’t do this.”

“You’re gonna be fine! Calm down, jeez. You look like a tomato.” Sam said and then picked up his pace so he could reach Cas. “Hey, Cas! How’s it goin’?”

“I’m having a wonderful day, thank you. And how was you’re day, Sam?” Cas asked, turning away from the car and towards Sam.

“Good. I mean, I didn’t ask out any long- standing crush of mine today, but I did ace a Chemistry test, so it’s been pretty decent.” Sam said, wincing as Dean elbowed him in the stomach.

“That’s good. Chemistry is an advanced class. You should be very proud that you’re doing so well.” 

“Yeah, Sam’s a marvel all right.” Dean said, mockingly, but with a hint of pride. “But I sorta forgot I have to drop him off at home, so we’ll have to do that before dinner, if that’s okay.”

Dean went around to the driver’s side of the car and unlocked the doors. After he climbed inside he noticed Sam entering the backseat, glaring and mouthing _Door._

_Shit. Probably should have opened the door for him. Focus, Winchester! You have to step up your game._

“That’s perfectly acceptable. I assumed you would want to take Sam home.” Cas said, sliding into the passenger seat.

The ride was oddly comfortable even though no one was making any particular conversation. Sam and Cas made small talk about school for a while, but mostly it was a silent drive. When they reached Dean’s house, he idled the car in the driveway while Sam got out.

“You two crazy kids have fun, alright? And be safe! Crack is whack. It gets better. Safe sex or no sex. All that jazz.” Sam yelled, walking away from the car under the weight of his backpack.

Dean groaned and hit his head gently against the steering wheel.

“One of these days, I’m going to purge myself off all the people I know and get new friends and family. Ones that don’t insist on butting into my life and making everything awkward.” Dean said, sighing and backing out of the driveway.

**Notes for the Chapter:**

> So, I've had this thing for forever and I don't really know where it's going. I basically just started it to make a whole bunch of references to the show and now it's all fluffy and I don't know where to take it. I am at a loss, but I will try my hardest to continue.
> 
> Also, I have a tumblr, in case that is something you wish to check out: glassestiel.tumblr.com
> 
> And, if you can't tell, I have a huge High School AU addiction. It is a problem. Judge me as you will.


End file.
